Synthesis of Aplyolide A, Ichthyotoxic Macrolide Isolated from the Skin of the Marine Mollusk Aplysia depilans

Aldo Spinella; Tonino Caruso; Marco Martino; Carmine Sessa

doi:10.1055/s-2001-18749

Synlett 2001; 2001(12): 1971-1973
DOI: 10.1055/s-2001-18749

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Synthesis of Aplyolide A, Ichthyotoxic Macrolide Isolated from the Skin of the Marine Mollusk Aplysia depilans

Aldo Spinella^* , Tonino Caruso, Marco Martino, Carmine Sessa

^*Dipartimento di Chimica, Università di Salerno, Via S. Allende, 84081 Baronissi (Salerno), Italy; Fax: + 39(89)965296; E-mail: spinella@unisa.it

Abstract

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A convergent pathway is described for the synthesis of (S)-aplyolide A (1) using ethyl (S)-lactate as chiral source. Key steps of the synthesis are two couplings between copper(I) alkynides and propargylic halides for the formation of skipped diyne systems and were performed with an improved procedure based on the use of cesium carbonate as base for alkynide preparation.

aplyolide A - natural product - macrocycles - total synthesis - alkynes

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